Images of Kimberly

Kimberly Wilder is a fabulous artist whose exquisite line drawings, generally in pencil, effect immediate penile erections or lubricated vaginas. Herself a transvestite, Kimberly's wild shemale art features transvestites young and old, the latter often putting the former through their paces as, using bondage and discipline techniques, including humiliation, spanking, forced feminization, and forced servitude, they train them in the fine art of being beautiful, feminine, desirable and submissive young ladies--or ladyboys--whose only purpose in life is to serve their harsh mistresses, anally, orally, and otherwise.

As I point out, in "Kimberly Wilder: An Assessment," as a boy, Kimberly played dress up and, tragically, she was sexually molested. Her traumatic experience is repeated, as it were, many times over, in the sexual abuse that her drawings' alter egos frequently suffer--and themselves, in turn, perpetuate upon others. In her art, Kimberly--that is, the surrogate for herself, the character who, created in her own image and likeness, bears an uncanny resemblance to the artist herself--both gives and receives abuse, experiencing both ends of the sadomasochistic spectrum of pain and pleasure. Like many other artists, Kimberly uses her talent to transcend the pain and suffering she endured in the past, making of these painful experiences the raw materials, as it were, of her present transformation of herself into a gorgeous transvestite and her celebration, in her beautiful drawings, of herself and all her experiences, past and present, pleasant and painful, alike.

Her drawings range from mild (or milder) to wild (or Wilder), featuring damsels in distress whose pain and suffering is produced by wealthy female sophisticates, Catholic nuns, demons, female employers, mothers, nurses, dominatrices, policewomen, female drill sergeants, and other female authority figures. It is rare that men inflict pain and suffering on Kimberly's cast of characters, but one drawing does show a beautiful, young ladyboy sandwiched between two black men with enormous erections. Usually, Kimberly's characters are tormented by older women, although, in some drawings, the abusers are the female (or shemale) peers of the humiliated victim.

As I observe, in "Kimberly Wilder: An Assessment," Kimberly is not only a gorgeous young ladyboy herself, but, in fact, the raven-haired, slender and statuesque transvestite, blessed with a classically beautiful face and a sexy figure, is frequently the model for the main characters in her own art. In this essay, I am evaluating the works in which the hairstyle, facial features, and figure of the protagonist makes it clear that this character is meant to represent Kimberly.

Kimberly appears as the protagonist in a drawing that shows her seated upon the edge of an office desk. Her hair is styled in the same manner that the artist wears her own hair, and the figure is wearing hoop earrings, a green jacket, a black skirt, blue-green stockings, and high-heeled shoes that match the jacket's color. Her arms are at her sides, the palms of her hands pressed flat against the desktop. Her skirt, which would fall to about mid-thigh, is pushed back, up her smooth, shapely legs, to reveal her cock, which juts, half-erect, from beneath the hem of the pushed-back skirt, a tangle of dark, coiled pubic hair visible just above the shaft. Her knees are together, but her feet are apart, and she stares straight ahead. Seated in an executive's swivel chair mounted upon a wheeled platform, a somewhat older woman, her hair in a bun adorned with a small red bow, wearing gold earrings, a light-pink shirt, a red ribbon tie, a dark-pink mini-skirt with thin black belt, a wristwatch, sheer pantyhose, and light-pink high-heeled shoes, the fingers of her right hand fanned out beneath her chin, gives Kimberly an appraising look, as if she is considering the lovely transvestite for more than a job, an impression that is reinforced by the image of a face that could be that of either a man or a woman sucking a cock on the executive's computer monitor's screen. If this drawing has a title, I'm unaware of it, but a perfect one would be "The Interview" or "Hired on the Spot." If a sexy look (and a flash of flesh) is a prerequisite to being hired, it seems safe to say that the stunning Kimberly will get the job!

Another drawing shows a completely different side of the artist's personality, as, a champagne glass in hand and wearing a black leather bodice, black leather gloves that ascend to the middle of her biceps, and stiletto-heeled, thigh-high boots, also of black leather, Kimberly straddles the hips of a young blonde who, wearing nothing but a pair of panties that have been pulled below her knees, stockings with fancy, ruffled tops, and high-heeled shoes, sprawls across a footstool, a cigarette in her left hand and a glass of bubbly in her right hand. Kimberly has just popped the cork on another bottle of champagne, and the cork is shown in mid-flight as, in its wake, a stream of the bottled beverage erupts, as if it were a copious jet of semen, from the neck of the bottle, which grasping , as if it were a cock, Kimberly has jammed, bottom-first, into the gaping anus of the blonde's skewered bottom, above the fair-haired young woman's own erect, downward-pointing prick. A title for this masterpiece of sadomasochistic partying might be either "Party Girls" or "Happy New Year's Eve!"

A third image of Kimberly shows her standing, facing one of the walls that forms, with another, the corner of a room. The wall behind her is dark; the other, which she faces, is light. The tail of her unbuttoned shirt is tied below her large, round, firm, high breasts, which, fully exposed, reveal themselves to be as lovely a pair as those of any genetic woman, and Kimberly is in the act of tugging the front of her unzipped jeans below her balls. Her massive, erect cock juts forth, veins thick and swollen beneath the taught flesh of the swollen shaft, in all its masculine glory, above the firm, risen ovals of her testes. Her shirtsleeves are rolled above her elbows, and, with the index finger of her right hand, she touches one of the three gobs of her own semen that decorates the wall before her. The wall bears a drawing of a Valentine's-shaped heart, pierced by an arrow, with one name written above it and another below, but the names, unfortunately, are illegible. Was this message--perhaps one written and drawn by Kimberly herself--the Kimberly in the drawing (as well as Kimberly the actual artist)--the inspiration for the ecstasy that has resulted in her ejaculation, as the dark-haired beauty recalled a past or present romance? Again, if the drawing has a title, it is unknown to me, although I think a suitable one for this picture might be "An Affair of the Heart" or "Romance Remembered."

I have commented, already, in "Kimberly Wilder: An Appreciation," upon a fourth of the drawings in which Kimberly herself seems to make an appearance, but, since this essay is concerned with the works of her art in which the artist herself appears as a character, I would be amiss if I did not repeat my observations about this drawing in this writing: In a work reminiscent of Rene Magritte's surrealistic painting, Attempting the Impossible, an artist, looking suspiciously like Kimberly herself, seems to put the finishing touches to a magnificent erection she is painting--an erection that juts through a hole in her canvas and onto the painting's surface. The canvas itself has been painted to resemble a wooden fence, so that the penis that the artist paints is both an imitation of an erect prick and the actual erection itself. The stiff, hard cock that she paints is mirrored by her own erection, so that this surreal masterpiece invokes questions, all at once, about the nature of art, the nature of reality, the nature of perception, and the nature of artistic inspiration.

In evaluating Kimberly's art that features a portrait of the artist herself, I prefer to cite only those in which the protagonist has dark hair cut in a fashion similar to Kimberly's own raven tresses, but a few of the beleaguered ladyboys in her drawings resemble her closely enough, even when their hair is not dark, to suggest that the character is intended to represent Kimberly. One such picture shows the lovely young ladyboy decked out in a peek-a-boo bra, stockings, and high-heeled shoes. Masturbating, she has reached the point of no return, and semen spews from the erect cock she grasps tightly in her right fist, the spray of her seed dashing against the wall in front of her. A butt plug falls from Kimberly's ass, the lubricant that had eased its insertion a splutter of thick droplets. Although Kimberly looks shocked and worried, if not, indeed, afraid, the two women standing in the open doorway behind her pay no attention to the ejaculating ladyboy as they chat away, the younger of them, who wears a dress much like the ones worn by mothers in 1950s situation comedies, smoking a cigarette as she leans casually against one side of the door frame, and her companion, an elderly woman whose sagging bosom is visible, like her slightly rotund tummy and her legs, through the sheer nightgown she wears with her pearl necklace and dainty heels adorned with small ribbons on their insteps. It seems as if the women have seen this same type of behavior many times before and they are neither shocked, titillated, nor even interested in it. It is only Kimberly who is distressed by the presence of the women. A good title for this apparently untitled work might be "Jaded Ladies" or "Needless Epiphany."

Kimberly also seems to put in an appearance in a picture that shows her introducing a pair of young ladyboy lovers to a somewhat older woman, whose buttocks Kimberly holds as she indicates the girly boys. Perhaps the matron is on a shopping spree, hoping to purchase one or both girls, or maybe one of them is her daughter, whom she has entrusted to Kimberly for feminization and training as a transsexual. As Kimberly chats with the older woman, the girly boys, one dressed in a sheer, frilly slip, panties with scalloped hems, knee-high stockings and high-heeled shoes, a bow in her short, flipped-under bob, and holding a small purse shaped like a Valentine's heart, seems about to French kiss the other, a pretty ladyboy peer who wears a sundress with a wide ribbon sash tied in a big bow at the back of her waist, panties, stockings and a garter belt, and high-heeled shoes. At the top of the left stocking, which faces the viewer, the name "Kimberly" is spelled out in a fancy, flowing script. However, the young woman--or transvestite--who chats with her visitor is also obviously Kimberly, as a young adult, so it appears that this drawing is privileged to depict not one, but two, images of the artist, one of her in her earlier years and the other of her as she appears at the point in her career that she actually drew this picture! Both images depict a lovely ladyboy, one blooming, the other in bloom. Together, these images of Kimberly perhaps represent the two aspects, the sadistic older and the masochistic younger version, of the same person. In any case, each ladyboy lover grasps her own erect, ejaculating penis, pressing its shaft and glans against the shaft and glans of the other transsexual's genitals, sharing both flesh and semen as preludes to the deep, wet kiss they apparently plan to enjoy. A good title for this drawing might be "Double the Pleasure" or "Kimberly, Now and Then."

Kimberly's work contains several other images of the artist, and, perhaps, in a future installment of my series of essays concerning Ms. Wilder, I will include descriptions of them as well. Now that I have cum--or come--across a picture that unambiguously identifies a younger woman as representing the artist as she appeared earlier in her life, I will also likely contribute an essay that touches upon that part of Kimberly's work that she devotes to portraits of herself as a younger ladyboy. Meanwhile, check out the artist's work online. It's fabulous and fine, just like Kimberly Wilder herself!